Hey Geoff,
No experience yet, but literally just bought a can yesterday to have a crack at it (possibly this Friday).
I'm in the same situation as you - need to do it out on the mooring, and I'm starting with the stern and working my way forward. Here's the deck prep I've done:
imgur.com/a/SdBPq so far. I was pretty concerned for the same sort of reasons - what about areas I couldn't get to easily etc, but I found this video:
where a guy goes back specifically to get to hard to reach places with a couple of homemade brushes and just stipples it on himself - seems like you should be able to do it, as long as you put on and equivalent amount of paint each time.
I'm really interested to see how many sins it will hide on mine - although I've done a fair bit of sanding and scraping, I'm no expert, so I'm hoping that the thickness of the kiwigrip will cover it up a bit!
I'll post some pics when I do get it done anyways - if you beat me to it, I'd love to see your before/after too!